Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging

• Get fluorescent glyco-BODIPYs by the combination of a Heck-like cross coupling and Knoevenagel condensation. The glycosidase stable BODIPY-mannose acts as efficient DC-SIGN targeting probes in vitro. BODIPY-mannose: high performant tool fluorescence STED microscopy. functional modular glyco-probe can be further functionalized with bioactive compounds. Significant perspectives on tracking lectin-mediated cell uptake diverse biological settings. Lectins are involved wide range carbohydrate mediated recognition processes. Therefore, availability highly tools tailored for lectin able to efficiently track events related such key targets is demand. We report here synthesis 1 2 , based condensation, which revealed addressing lectins. In particular, glyco-BODIPY has two C-mannose residues, act (dendritic cell-specific intercellular adhesion molecule-3-grabbing non-integrin) modules. By using live-cell microscopy, we proved that was taken up immune cells expressing receptors. Super-resolution stimulated emission depletion (STED) microscopy internalized localized membranes endosomes, proving reliable also applications. Of note, contains an aryl-azido group, allows functionalization glycoprobe molecules, thus paving way use internalization